Leonardo DiCaprio's Cringey Midlife Crisis Moments Don't Do His Soured Reputation Any Favors

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Despite his demonstrable success, Leonardo DiCaprio has been quietly losing popularity in recent years. Over the first two decades or so of his career, the Oscar-winning actor gifted us hit after hit, going from "Titanic" to "Catch Me If You Can" to "The Wolf of Wall Street." In a 2013 interview with German publication Bild, DiCaprio acknowledged feeling burnt-out, confirming, "I am a bit drained. I'm now going to take a long, long break. I've done three films in two years, and I'm just worn out. I would like to improve the world a bit," (via NME). In the meantime, the former child star intended to focus on his environmental activism. While DiCaprio's onscreen appearances became few and far between, he worked behind the camera as a producer. At one point, DiCaprio narrated a documentary that most people didn't know about. 

Unfortunately, also during the break, DiCaprio's reputation was ruined as the world learned of his many shady behaviors over the years. In the past, the beloved actor had always been able to rely on his environmental work to give him some good publicity. However, even DiCaprio's extensive efforts for the cause came into question as reports suggesting that he was a regular private jet user emerged. Considering this, it's unsurprising that the once-untouchable Hollywood star seemingly started having a midlife crisis. When we shared some cringey moments from this time with Amy Prenner, a communications expert and the founder of The Prenner Group, she had some thoughts on how the actor could get back into the public's good books again, most of which involve simply, "show[ing] growth and some maturity."

Leonardo DiCaprio's 49th birthday bash in November 2023 was a star-studded event that included the attendance of Beyoncé, Jay-Z, and Kim Kardashian, alongside many other A-listers. In a chat with People, an insider shared that the attendees of the lavish Beverly Hills party kept their energy up until 4 a.m. Further, they revealed that DiCaprio even got the rock star treatment during the celebrations and was "raised and carried around the room." The celebrity attendees belted out classic hip-hop songs at one point too. It was apparently in that moment that the "Titanic" star decided to revel in all the attention and rap Gang Starr's "DWYCK" featuring Nice-N-Smooth. 

pic.twitter.com/NZTyY7REVd

— Videosareforever99 (@videosaregood) November 14, 2023

Although his pals hyped the birthday boy up as he poured his heart and soul into the rap, people watching at home cringed over the footage. Some Redditors were reminded of a scene from HBO's "Succession," when Kendall Roy puts on a similarly cringey performance of "L to the OG" for his father, Logan Roy. Likewise, one commentator was reminded of Justin Timberlake's infamously cringey interaction with Ginuwine: "Oh yeah, fo' shiz, fo' shiz. Ginuwine! What's up, homie?"

Another critic remarked, "Leo is literal proof that your growth gets stunted at the age you become famous." Notably, several other commentators couldn't see what all the fuss was about, believing that DiCaprio was simply living it up at his birthday party, like anybody else would. One commentator summed up the other side's perspective in one sentence: "How dare a grown man have fun."

In March 2025, Leonardo DiCaprio made a desperate attempt to stay relevant with the younger generations by making a YouTube channel. The Oscar-winning actor started his journey by sharing the trailer for his film "One Battle After Another." Although it initially seemed like the channel's creation may have been a means for DiCaprio to promote his upcoming movie, we quickly learned that wasn't the case. In the following months, the "Departed" star used his massive following for good by drawing attention to the efforts against allowing oil exploration in Africa's Okavango River Basin, and the importance of protecting the Southeast Alaska Tribe against urbanization efforts. Unfortunately, most of his videos underperformed, with many only receiving a paltry couple of thousand of views even months after their release. 

Additionally, commentators on X, formerly known as Twitter, poked fun at DiCaprio's foray into YouTube. As expected, there were several jokes about how he would incorporate his distaste for anything over 25 into his videos. While one user suggested that the star would go ballistic if his subscriber counter exceeded 25, another quipped, "He will be posting a 'GRWM to date women under 25 yrs old' videos." One person even posited that the "Romeo + Juliet" star had started a YouTube channel solely to get easier access to much younger women. Unfortunately, even the content of his channel wasn't enough to convince people that he had the best of intentions. When one Redditor pointed out that DiCaprio was using his platform to promote environmental conservation, another snarked, "Posting from his yacht I bet. Conservation my a**."

For some, Leonardo DiCaprio's most scandalous age gap relationships have left no room for doubt that he is going through some kind of a midlife crisis. Most of the nineties star's girlfriends over the years have shared two noticeable similarities: They were all models who are at least a decade younger than him. Still, DiCaprio's romance with Vittoria Ceretti managed to cause even more of a stir because she's 24 years younger than him. Before her, then-43-year-old DiCaprio had a nearly 5-year-long relationship with Camila Morrone, who was 22 years his junior. 

In 2022, an insider dished to the New York Post the reason why the Oscar winner preferred to date women in their early twenties: "By the time girls reach 25, they're looking for more — they're looking to get married and settle down." They continued, "That is not what Leo wants. He does not want a family and does not want to be around women who may press him for that." The source also disclosed some other dating non-negotiables that DiCaprio supposedly had, including keeping his girlfriends at arm's length. 

Moreover, according to supermodel Gisele Bündchen, who was one of DiCaprio's most high-profile failed relationships, his refusal to grow up started far sooner than the public realized. In Bündchen's 2018 memoir "Lessons: My Path to a Meaningful Life," she shared that when she was 25, she was forced to end her 5-year relationship with then-30-year-old DiCaprio because she realized that she needed to break out of her unhealthy coping mechanisms, while he wanted to stay the same.

Leonardo DiCaprio accidentally admitted that he was insecure about his affinity for age gap romances in a 2025 Esquire interview with filmmaker Paul Thomas Anderson. When the director questioned how old the actor felt he was, DiCaprio replied, "32." Moreover, the then-50-year-old didn't push back when Anderson opined that his emotional age was 32. When asked whether he was reflecting back on his life after half a century of existence, the "Killers of the Flower Moon" star replied, "Well, it creates a feeling like you have a desire to just be more honest and not waste your time. I can only imagine how the next few decades are going to progress." Further, DiCaprio stressed that he had no desire to "waste [his] time" on professional and personal relationships that didn't serve him anymore. 

Unfortunately, DiCaprio's enjoyment of his time has occasionally made people cringe. Netizens were reacting uncontrollably when they saw a video of DiCaprio busting a move to Charli XCX and Troye Sivan's "Talk Talk" at a 2024 event. The actor's attempts to cling to his youth apparently didn't do him any favors, leaving one Instagram commentator to remark, "Old [man] vibes ....," and another to quip, "Ok whatever Dad." We saw the activist engaging in another attempt to hide his true age when he attended CinemaCon 2025 in April. The star had dyed his hair and eyebrows a much darker color and adopted a tinted beard in an apparent attempt to keep his grays concealed. Unfortunately, DiCaprio's appearance at Wimbledon 2025 further proved that his reputation would likely never recover.

Leonardo DiCaprio watching Charli xcx & Troye Sivan perform their 'Talk talk' remix at the 2024 LACMA Art+Film Gala in Los Angeles. pic.twitter.com/PIRurclZ4h

— xcxshake (@xcxshake) November 4, 2024

Exclusively speaking to The List, communications expert Amy Prenner offered some insight into the ways in which Leonardo DiCaprio could turn the page on his soured reputation. She started by proclaiming that a person's public image wasn't solely centered around their philanthropic and professional work, but their personal life as well. Additionally, Prenner felt that the many shady rumors about DiCaprio could overshadow the image he has built through his critically acclaimed work. The expert went on to suggest the ideal path towards positively changing his public image: "If he wants to shift that narrative, he doesn't need to reinvent himself, but he does need to show growth and some maturity." Prenner further explained that this was the right move for the climate activist because audiences adored someone who could be real while still continuing to evolve. 

A great starting point for DiCaprio would be to take a younger actor under his wing and mentor them using his Hollywood expertise. The nineties icon could further benefit from breaking the strictly tight-lipped stance he has maintained throughout his career and poking fun at all the stereotypes associated with him. Ultimately, the expert professed that DiCaprio was better off realizing that authenticity didn't necessarily mean that he had no room to change. "It's about being comfortable enough in who you are today that the public can take you seriously, even when you're having fun," she said. "That balance is what will ensure his legacy isn't just about staying young but also staying relevant."